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Search for "sulfonamides" in Full Text gives 99 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

  • M. Fernanda N. N. Carvalho,
  • Rudolf Herrmann and
  • Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

Graphical Abstract
  • supported by the IR spectrum. Only one S=O vibration can be identified at 1098 cm−1, in a similar position as the S=O vibrations in DMSO (1050 cm−1) or tert-butylsulfinamide (1032 cm−1) [43]. The strong band at about 1330 cm−1, typical for the asymmetric S=O stretch in sulfonamides and sulfones, is absent
  • groups, but there is a medium intense C=C stretching vibration at 1653 cm−1 and two strong bands at 1324 cm−1 and 1059 cm−1 for the asymmetric and symmetric stretches of the O=S=N moiety. Compared to the SO2 moiety in sulfonamides (e.g., 21b with 1330 cm−1 and 1128 cm−1) the symmetric stretch is at
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Published 26 Jun 2017

DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support

  • Johnny N. Naoum,
  • Koushik Chandra,
  • Dorit Shemesh,
  • R. Benny Gerber,
  • Chaim Gilon and
  • Mattan Hurevich

Beilstein J. Org. Chem. 2017, 13, 806–816, doi:10.3762/bjoc.13.81

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  • introduction of the o- or p-nitrobenzenesulfonyl groups to primary amines in the first step. The semi-protected sulfonamides can then undergo a selective mono-methylation via Mitsunobu reaction or by direct methylation. The reaction is completed by the selective removal of the sulfonamide group. Miller and
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Published 03 May 2017

Transition-metal-catalyzed synthesis of phenols and aryl thiols

  • Yajun Liu,
  • Shasha Liu and
  • Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

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  •  41). The regioselectivity was maintained in the presence of various functional groups. Further studies revealed that several functional groups such as esters, amides and sulfonamides could be added to the list of directing groups. The Dong group reported a similar work and developed two types of
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Published 23 Mar 2017

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

  • Ramana Sreenivasa Rao and
  • Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

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  • in 30 minutes from 7a. While increasing the reaction time from 30 minutes to 2 h, the formation of biologically active pyrazinone 10a has been realized as a major product along with ene-diamide 9a. A literature survey revealed that sulfonamides are known to undergo hydrolysis in the presence of a
  • Brønsted acid [32]. Sulfonamides also participate in amide hydrolysis with external nucleophiles such as phosphide anions [33] or phenyldimethylsilyllithium [34]. The combinations of thiophenol/K2CO3 [35] or NaOH/MeOH [36] are also known to hydrolyse sulfonamides. These methods lead to the formation of the
  • corresponding free amines. Such desulfonylation of sulfonamides has been less utilized to make an unsaturated bond, for example, imine. Hence, attention has been paid to find suitable conditions for the formation of pyrazinones directly from piperazine-2,6-diones via cyclization followed by dehydrosulfonylation
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Published 07 Mar 2017

A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

  • Arno Verlee,
  • Thomas Heugebaert,
  • Tom van der Meer,
  • Pavel I. Kerchev,
  • Frank Van Breusegem and
  • Christian V. Stevens

Beilstein J. Org. Chem. 2017, 13, 303–312, doi:10.3762/bjoc.13.33

Graphical Abstract
  • amines, a decrease in substrate concentration was essential to selectively obtain amides over sulfonamides. It was shown that the procedure can easily be used for the synthesis of a compound library suitable for initial screening; and that the optimized synthetic conditions are directly transferrable
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Published 16 Feb 2017

Chromium(II)-catalyzed enantioselective arylation of ketones

  • Gang Wang,
  • Shutao Sun,
  • Ying Mao,
  • Zhiyu Xie and
  • Lei Liu

Beilstein J. Org. Chem. 2016, 12, 2771–2775, doi:10.3762/bjoc.12.275

Graphical Abstract
  • ) was selected as the model reaction for optimization employing Kishi’s oxazoline/sulfonamides as the chiral ligands. A series of oxazoline/sulfonamide ligands (L1–L8) were tested and the results were summarized in Table 1. Four subgroups of R1 were studied (entries 1–4, Table 1) and isopropyl
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Published 19 Dec 2016

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

  • Kevin Lafaye,
  • Cyril Bosset,
  • Lionel Nicolas,
  • Amandine Guérinot and
  • Janine Cossy

Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241

Graphical Abstract
  • including alcohols, halides, esters, amides, carbamates and sulfonamides are compatible with the metathesis conditions [14][15][16][17][18][19][20]. However, the involvement of alkenes containing a nitrogen atom such as an amine or an N-heteroaromatic ring in metathesis reactions is still problematic and
  • allow the use of primary and secondary amines in ring-closing metathesis (RCM) and cross-metathesis (CM), and one of them is the transformation of amines into carbamates, amides or sulfonamides [27][28][29]. As an alternative, metathesis reactions can be performed with olefins possessing ammonium salts
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Published 18 Nov 2015

Recent advances in copper-catalyzed C–H bond amidation

  • Jie-Ping Wan and
  • Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

Graphical Abstract
  • adjacent to oxygen via an N-halosuccinimide- (NCS or NBS)-assisted copper-catalyzed process. As shown in Scheme 2, both cyclic and acyclic compounds 6 containing a benzylic C–H bond could be readily converted to N-alkylamides 8 or sulfonamides 9 via this much milder catalytic method. In addition, this
  • or secondary sulfonamides 15 with the assistance of 1,10-phenanthroline as a ligand (Scheme 3). Notably, the asymmetric version of a similar amidation had been previously achieved by Clark et al. via copper catalysis in the presence of a chiral oxazoline ligand, which allowed the synthesis of
  • reaction at 100 °C allowed the synthesis of various N-alkylamides, sulfonamides and imides with fair to excellent yield, and the results also suggested that the catalytic method tended to selectively enable the transformation of secondary or primary C–H bonds, while the amidation of the tertiary alkyl C–H
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Published 17 Nov 2015

Recent applications of ring-rearrangement metathesis in organic synthesis

  • Sambasivarao Kotha,
  • Milind Meshram,
  • Priti Khedkar,
  • Shaibal Banerjee and
  • Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

Graphical Abstract
  • catalyst 7. Pyrrolines were produced in excellent yields by RRM of sulfonamides 31a,b using the catalyst 2 under dichloromethane reflux conditions (32a 99%, 32b 70%) (Scheme 3). Five-membered heterocycles such as 34 and a seven membered heterocycle 35 in 40:60 ratio (97%) were formed by RRM of
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Published 07 Oct 2015

Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides

  • Hanmo Zhang,
  • E. Ben Hay,
  • Stephen J. Geib and
  • Dennis P. Curran

Beilstein J. Org. Chem. 2015, 11, 1649–1655, doi:10.3762/bjoc.11.181

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  • Hanmo Zhang E. Ben Hay Stephen J. Geib Dennis P. Curran Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA 10.3762/bjoc.11.181 Abstract Two new fates of imine intermediates formed on radical cyclizations of ene-sulfonamides have been identified, reduction and hydration
  • ; radical cyclization; radical fragmentation; spiro-indoles; Introduction Radical additions and cyclizations of ene-sulfonamides are useful reactions in a number of settings. The primary products of these reactions, α-sulfonamidoyl radicals, are often thought to undergo elimination reactions of sulfonyl
  • radicals to make transient imines [1][2][3]. In turn, onward reactions of the imines provide assorted products including ketones and nitrogen heterocycles [4][5][6][7][8][9][10]. Figure 1a shows a generic addition/elimination reaction of ene-sulfonamides along with example transformations in Figure 1b from
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Published 17 Sep 2015

Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

  • Gerold Heuger and
  • Richard Göttlich

Beilstein J. Org. Chem. 2015, 11, 1226–1234, doi:10.3762/bjoc.11.136

Graphical Abstract
  • has been achieved by Zhang [22] using copper or palladium catalysts and proceeds via radicals and fluoropalladation, respectively. Cyclisation reactions of unsaturated sulfonamides which proceed via amidyl radicals have been described by Li [23] and by Oshima [24]. Chemler [25][26] discusses radical
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Published 21 Jul 2015

Azobenzene-based inhibitors of human carbonic anhydrase II

  • Leander Simon Runtsch,
  • David Michael Barber,
  • Peter Mayer,
  • Michael Groll,
  • Dirk Trauner and
  • Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

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  • University Munich and Munich Center for Integrated Protein Science, Lichtenbergstr. 4, 85748 Garching, Germany 10.3762/bjoc.11.127 Abstract Aryl sulfonamides are a widely used drug class for the inhibition of carbonic anhydrases. In the context of our program of photochromic pharmacophores we were
  • interested in the exploration of azobenzene-containing sulfonamides to block the catalytic activity of human carbonic anhydrase II (hCAII). Herein, we report the synthesis and in vitro evaluation of a small library of nine photochromic sulfonamides towards hCAII. All molecules are azobenzene-4-sulfonamides
  • , that leads to blindness, is achieved with the application of aryl sulfonamides [3]. Being a transition-state analogue [4], this functional group exhibits excellent blocking characteristics of hCAII and culminates its power in many modern marketed drugs, such as acetazolamide (AAZ) or dorzolamide
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Published 07 Jul 2015

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

  • Katherine M. Byrd

Beilstein J. Org. Chem. 2015, 11, 530–562, doi:10.3762/bjoc.11.60

Graphical Abstract
  • and co-workers developed various N-sulfinyl homoallylic amines (76) [160] and N-cinnamyl sulfonamides (77) [161] ligands for the rhodium-catalyzed asymmetric 1,4-arylation of a variety of α,β-unsaturated carbonyl compounds. Finally, in 2012, Franzén and co-workers designed an indole-olefin-oxazoline
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Published 23 Apr 2015

A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides

  • Antoine Pignon,
  • Erwan Le Gall and
  • Thierry Martens

Beilstein J. Org. Chem. 2014, 10, 425–431, doi:10.3762/bjoc.10.39

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  • Antoine Pignon Erwan Le Gall Thierry Martens Électrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS, Université Paris-Est Créteil, 2-8 rue Henri Dunant, 94320 Thiais, France 10.3762/bjoc.10.39 Abstract The synthesis of (diarylmethyl)sulfonamides and
  • related compounds by a new manganese-mediated, cobalt-catalyzed three-component reaction between sulfonamides, carbonyl compounds and organic bromides is described. This organometallic Mannich-like process allows the formation of the coupling products within minutes at room temperature. A possible
  • mechanism, emphasizing the crucial role of manganese is proposed. Keywords: carbonyl compounds; cobalt; manganese; multicomponent reaction; organic bromides; sulfonamides; Introduction (Diarylmethyl)amines constitute an important class of pharmacologically active compounds, displaying e.g. antihistaminic
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Published 17 Feb 2014

New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions

  • Helge Klare,
  • Jörg M. Neudörfl and
  • Bernd Goldfuss

Beilstein J. Org. Chem. 2014, 10, 224–236, doi:10.3762/bjoc.10.18

Graphical Abstract
  • , e.g. sulfonamides [12], urea-N-sulfoxides [13], guanines [14] as well as protonated catalysts such as ammonium [15], 2-aminopyridinium [16] and guanidinium [17] motifs. Most catalysts can form two hydrogen bonds to a reactant, which further enhances their ability to activate and constrain it to a
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Published 21 Jan 2014

Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

  • Lisa Moni,
  • Luca Banfi,
  • Andrea Basso,
  • Alice Brambilla and
  • Renata Riva

Beilstein J. Org. Chem. 2014, 10, 209–212, doi:10.3762/bjoc.10.16

Graphical Abstract
  • reactions [2], especially the intramolecular Mitsunobu reaction of alcohols with phenols or sulfonamides. By exploiting a single post-MCR transformation (the Mitsunobu reaction) it is possible to obtain several diverse heterocyclic scaffolds by installing the two additional groups in any of the four
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Published 17 Jan 2014
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  • ; rheology; sulfonamides; Introduction Various diepoxides easily react with amines or diamines to form cross-linked, cyclic or linear addition-polymers, which are implemented in construction, electronic, aerospace, medical and dental industries [1][2]. Hereby, bisphenol A diglycidyl ether (BADGE) is often
  • [16][17][18]. To our best knowledge, CD mediated N-alkylation of sulfonamides is not yet described. Generally, only a few examples are known in literature about CD assisted alkylation of amines in aqueous solution [19][20][21][22]. Hence, in this work, we wish to present our direct and CD mediated
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Published 09 Dec 2013

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

  • Christina Lohoelter,
  • Malte Brutschy,
  • Daniel Lubczyk and
  • Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

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  • Triphenylene ketals The high hydrogen bonding donor capability of sulfonamides made this class of functional groups highly attractive for supramolecular affinity materials [60]. The installation of larger substituents at the sulfonyl moiety should provide suitable properties for the processing on the quartz
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Published 09 Dec 2013

New developments in gold-catalyzed manipulation of inactivated alkenes

  • Michel Chiarucci and
  • Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

Graphical Abstract
  • addition of carbamates, sulfonamides and imidazolidinones to linear and cyclic dienes 17 in the presence of catalytic amounts of PPh3AuOTf (Scheme 6). The method featured excellent 1,2-regioselectivity and high chemoselectivity, providing protected allylamines 18, in good yields, using nearly equimolar
  • extended to amide-based nucleophiles exploiting similar operational conditions [39]. After these seminal works the scope of gold-catalyzed hydroamination of olefins was extend to other classes of nitrogen nucleophiles. Sulfonamides were successfully employed in the intra- and intermolecular hydroamination
  • of alkenes catalyzed by Ph3PAuOTf (toluene, 85 °C, Scheme 8) [40]. In particular, primary and secondary sulfonamides reacted smoothly with mono and disubstituted alkenes delivering nitrogen compounds 22 and 23 with Markovnikov regioselectivity (Scheme 8a). Moreover, N-protected pyrrolidines 24 and 25
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Published 21 Nov 2013

The chemistry of amine radical cations produced by visible light photoredox catalysis

  • Jie Hu,
  • Jiang Wang,
  • Theresa H. Nguyen and
  • Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

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  • Marvin group reported an identical synthesis of isoquino[2,1-a][3,1]oxazine using Ru(bpy)3Cl2 instead [88]. The tethered nucleophiles, primary alcohols or sulfonamides, are part of the N-aryl group of tetrahydroisoquinolines 73. Similar to the synthesis of tetrahydroimidazoles 72, MeOH was the optimal
  • amides. Intramolecular interception of iminium ions by sulfonamides. Intramolecular interception of iminium ions by alcohols and sulfonamides. Intermolecular interception of iminium ions by phosphites. Photoredox-catalyzed oxidative phosphonylation by Eosin Y. Conjugated addition of α-amino radicals to
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Published 01 Oct 2013

Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles

  • Wantanee Sittiwong,
  • Michael W. Richardson,
  • Charles E. Schiaffo,
  • Thomas J. Fisher and
  • Patrick H. Dussault

Beilstein J. Org. Chem. 2013, 9, 1526–1532, doi:10.3762/bjoc.9.174

Graphical Abstract
  • require relatively high temperatures [28][29][30]. Our results suggest that amines and amides actively suppress the ability of Re(VII)-oxides to activate alcohols. We note, however, a recent report by Ghorai describing the allylation of iminium ions generated from aldehydes and sulfonamides in the
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Published 30 Jul 2013

Gold-catalyzed intermolecular hydroamination of allenes with sulfonamides

  • Chen Zhang,
  • Shao-Qiao Zhang,
  • Hua-Jun Cai and
  • Dong-Mei Cui

Beilstein J. Org. Chem. 2013, 9, 1045–1050, doi:10.3762/bjoc.9.117

Graphical Abstract
  • the intermolecular hydroamination of allenes with sulfonamides is shown. The reaction proceeded smoothly under mild conditions for differently substituted allenes giving N-allylic sulfonamides in good yields with high regioselectivity and E-selectivity. Keywords: allene; gold catalysis
  • hydroamination, many require extreme and extended reaction conditions. Thus, development of these reactions is still needed. Recently, Yamamoto and co-workers reported the Pd(0)-catalyzed intermolecular hydroamination of allenes with sulfonamides [25]. In this paper, we wish to develop a gold(I)-complex
  • -catalyzed addition of sulfonamides as the amine partner to allenes to synthesize N-allylic sulfonamides with high regio- and stereoselectivity. Results and Discussion As part of our ongoing studies on metal-catalyzed reactions, we have reported the hydroalkoxylation of allenes with alcohols and
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Published 29 May 2013

Use of 3-[18F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

  • Reik Löser,
  • Steffen Fischer,
  • Achim Hiller,
  • Martin Köckerling,
  • Uta Funke,
  • Aurélie Maisonial,
  • Peter Brust and
  • Jörg Steinbach

Beilstein J. Org. Chem. 2013, 9, 1002–1011, doi:10.3762/bjoc.9.115

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  • sulfonamides was confirmed chromatographically by comparison with their nonradioactive counterparts. Even for weakly nucleophilic amines such as 4-nitroaniline the desired radiolabelled sulfonamides were accessible in satisfactory yields owing to systematic variation of the reaction conditions. With respect to
  • of the analogous fluoroacetamide. Keywords: fluorine-18; hydrolytic metabolism; prosthetic groups; radiochemistry; sulfonamides; Introduction The importance of molecular imaging, i.e., the characterisation and measurement of biological processes in living organisms at the molecular level using
  • desired intermediate was purified by vacuum distillation or transformed as crude product to the final 3-fluoropropanesulfonamides, as shown for compound 11. Alternatively, 10 was obtained commercially. The reaction of 10 with aliphatic amines proceeded quantitatively and smoothly to the sulfonamides 12–15
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Published 27 May 2013

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

  • Tamashree Ghosh,
  • Abhishek Santra and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

Graphical Abstract
  • preparation of several glycosyl donors such as thioglycosides [33][34], glycosyl sulfenamides [35] and sulfonamides [36], glycosyl disulfides [37], glycosyl thionolactones [38], etc. A number of reports are available for the preparation of glycosyl thiols, which include (a) a two-step reaction of glycosyl
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Published 22 May 2013

Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

  • Martina Bonsignore,
  • Maurizio Benaglia,
  • Laura Raimondi,
  • Manuel Orlandi and
  • Giuseppe Celentano

Beilstein J. Org. Chem. 2013, 9, 633–640, doi:10.3762/bjoc.9.71

Graphical Abstract
  • -established methodology to perform enantioselective reductions of carbon nitrogen double bonds [1]. In the past decade different classes of enantiomerically pure Lewis bases have been developed, including N-formyl derivatives, oxazolines, imidazole derivatives, sulfonamides and picolinamides [2][3]. Some of
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Published 02 Apr 2013
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